Date: Mon, 30 Jul 2007 09:31:38 -0700
From: Wolf pomo
Subject: Caning Freddy (gay / authoritarian, m/m)
DISCLAIMER:
This story is a work of fiction and contains
descriptions of explicit sexual acts of boy's
discovering their sexuality. It contains graphic
scenes of sex between an underage boy and adult
males... If this type of content offends you or you
are under the age of 18 do not read it.
Author's Note:
This story is the property of the author. It can be
downloaded for personal reading pleasure or sending
to a friend, but if you wish to re-post them at your
own site, please contact the author for permission.
If it is illegal to read such material where you live or
if you find the topic deceitful the please leave now.
If you enjoy the story or if it evokes memories of
your own, please let me know. I am happy to write
stories from outlines.
Copyright 2007 Wolf, All Rights Reserved.
You may contact me at whitewold999@icqmail.com if
you like. All flames will be ignored.
Caning Freddy
By
Wolf
It all started when Freddy moved up from
middle school to upper school. He was sent to a
boarding school for the first time when he was 16-
years old. That was the first time he was to be away
from home. He was assigned a roommate named
Charles.
He thought Charles was a nice enough guy. It
was also his first time away from home. He was a
little taller than Freddy. T
Their room consisted of two desks facing the
windows over looking the common, closets on either
side of the door and bunks with storage drawers
under them. They had to walk all the way down the
hall to the bathroom and showers.
It took them a little while to get used to each
other. They had been placed in the same room
because they were both majoring in Civil Engineering.
They both had dreams of building bridges and roads
in some exotic places like Australia.
They were both kind of shy around each other
at first. They would not even look at each other
while getting dressed in the morning or as they got
undressed for bed.
Freddy was a normal boy. He had discovered
the joy's of wanking when he was about 12-years old.
He didn't do it in their room for fear of being caught
for the first few weeks. He had tried dating girls in
lower school and did not like them.
One was all over him wanting him to stick his
fingers in her pussy and lick her pussy before he
could fuck her. When he put his finger in her pussy
he could smell it and he thought she stank. He almost
vomited when she stuck her pussy in his face begging
him to suck her pussy. He was not even able to get a
boner so he never fucked her. Then one of the older
boys in school became his friend.
This boy was a couple of years older. He
introduced him to mutual masturbation. When they
were wanking each other daily the guy taught him how
to suck cock. He also sucked a few other cocks in
lower school. It all seamed so natural. He knew that
he would always prefer boys to girls.
As much as he wanted to find out if Charles
would like his cock sucked he was afraid to broach
the subject. The changing point came when Charles
announced that he was going to the library to do some
research.
Shortly after he left the room Freddy could not
stand it any longer and flopped on his bed after
pulling his pants and knickers down to his knees. He
took his tool in hand and started wanking. When he
heard the key in the door he could not get his pants
up fast enough. Charles entered the room and saw
him lifting his ass trying to pull his pants up. Of
course he was fully exposed and erect.
He closed the door behind himself and said,
"What a relief. I am a wanker too. I have been going
crazy wanting to jack-off."
Freddy had never seen him doing it. They
talked about it for awhile, rather nervously.
Eventually they agreed to masturbate each other.
Charles squeezed onto the bunk next to Freddy after
he had pulled down his pants. They were both
circumcised. They each took hold of each other's
cock and started pulling on them. Freddy found out
that Charles' cock was a little longer and thicker than
his own. Charles didn't object when he leaned over
his body and started sucking his cock. Charles
returned the favor after he climaxed in Freddy's
mouth. They started making it a practice of jacking-
off and sucking each other every night after that.
Most of the other boys in the school went home
on the weekends. Freddy and Charles parents lived
to far away to make the trip very often. They opted
to stay in the dorm on weekends. They had the floor
to themselves on weekends. They could pretty much
lounge around the floor naked if they chose.
They could sleep in Saturday. One such day
Charles got out of his bed and mounted Freddy in a
69. They sucked each other until they came. When
Charles sat up his asshole was rubbed against
Freddy's face.
Freddy loved the smell and could not resist
licking his brown hole. Not only Charles enjoyed the
experience. Freddy found that he loved the smell of
his asshole and reaming Charles.
It was only fair that Charles tongue fuck
Freddy's asshole too. If he didn't enjoy it he never
let on that he would not do it.
Later in the academic school year Charles
proposed to Freddy that he allow him to try and fuck
his asshole. Freddy was willing to try and they spent
an entire Saturday experimenting with a variety of
positions. Chuck would cover his cock with a lubricant
and try to get it into Freddy's asshole but each time
they tried it hurt too much. The way they finally got
it in was for Freddy to bend over one of the two
chairs and hang onto the arms of the chair and placed
one knee on the seat. Charles stood behind him and
held onto his hips as he thrust his hips forward. It
hurt like hell until Charles started fucking him.
Freddy could not believe the way his own cock
swung back and forth while being fucked. He had the
largest boner of his life. All Chuck had to do was
reach around and pull on it one time and Freddy shot
his load of cum all over the seat of the chair.
It took a little time for Freddy to get used to
being fucked but eventually he was able to take all of
Chuck's cock any time they wanted to fuck. Freddy
preferred to lay face down on the bunk with a hard
pillow under his hips to elevate his ass for Chuck.
They had agreed to not cheat on each other and
they didn't like condoms. They both thought it felt
better without rubber. They like direct contact, skin
against skin.
They did it sitting in their study chairs with
Freddy facing him and with his back to Chuck.
Freddy loves the feeling of Chuck's cum leaking out of
his asshole. He reached between his legs and wipes
his asshole so that he can taste Chuck's cum right
from his own asshole.
It was Chuck's nightly habit to cum in Freddy's
ass and leave it in there until it went soft and just
flopped out. Freddy would take his spent cock in his
mouth after he had just fucked him and suck him
clean. He was in his glory when he could make Chuck
hard again so that he could fuck him again. It was
great to take his limp cock into his mouth and suck
him until he had another raging hard-on. It was not
uncommon for them to fall asleep with Chuck's cock in
his ass after the second fucking.
They looked forward the weekends when they
would have the place to themselves. They would only
leave their room when they had too. One morning
when Chuck was ready to go get something to eat and
Freddy was being lazy he slapped with a leather belt
him across the butt as he lay face down on the bed
feigning sleep. He had doubled his belt before
spanking Freddy. It was meant to be playful but it
stung Freddy.
The strange thing was Freddy felt his cock
come alive and it pressed against the cot hard.
Freddy pleaded with Chuck to do it again. Chuck got
a wicked look on his face and slapped Freddy's ass
again, a little harder this time. With each stroke
Freddy felt hornier. On the tenth stoke Freddy
actually climaxed. Even Chuck saw the wet spot
between Freddy's legs on the sheet. As Far as
Freddy was concerned it was the best climax he had
ever had. The thing that made it even better was
Chuck mounted his red ass and fucked him one more
long hard tiring time.
The first thing Freddy did was go out and buy
them a cane. He selected one about a meter long. It
was thin and flexible while being stiff. Charles was
thrilled and after that on weekends he would punish
Freddy. Freddy would bend over to present his bare
bum and Chuck would start at the small of the back
and lay stripes down his ass to the backs of Freddy's
thighs. Just before Fucking Freddy's ass he would
slap Freddy's scrotum. The first weekend he caned
Freddy and fucked him between 6 and 8 times. The
caning and fucking had been so thorough that Freddy
had to take three days off from school. He could not
lie on his back or sit in a chair. He even had to take
his dumps squatting over the toilet.
Chuck tried to apologies time and time again but
Freddy assured him that it had been the best time of
his life. Over the years they had to buy a cane fairly
often because after several months of use the cane
would be frayed and limp if not broken. Canes just
don't last that long. Freddy loves the swishing sound
and the anticipation of the sting as the cane
descends on his bum. A slap of the genitals and
nipples also sends a thrill through his sexual organ.
They reserved the caning for the weekends
when they had the floor to themselves. They vary
the canings from severity from mild to hard between
having anal sex. The two of them could manage 4 or 5
rounds of anal sex and canings. In fact Freddy got so
he could not enjoy anal sex without being caned or at
least having a leather belt stripping his butt.
Freddy is normally the recipient but sometimes
as a variety Chuck would allow Freddy to cane him.
Freddy developed a strong taste for the caning to
start at the small of his back and work down his butt
and the backs of his thighs to the knees. By the time
the backs of his knees are turning red Freddy has
had at least two orgasms. After his backside is
bright red is when Freddy enjoys it the most when
Chuck mounts him. Chuck likes a slow pace, taking
long full strokes and never takes his organ out of
Freddy's anus until he ejaculation and his cock looses
his erection, it goes limp and just slips limply out of
Freddy's ass. It takes about an hour for Freddy to
recover afterwards. But then he is ready to start all
over again.
Keeping the canings to just weekends kept their
relationship from the other students but because
they were so close there was always the joking
speculation about their relationship. In the showers
they would tease them about which one was on top.
Freddy took the most teasing because he was the
more subservient of the two.
Freddy and Charles are twenty years old now
and about to finish their schooling. It seems almost
impossible that they were never discovered but they
managed to keep their classmates from conferring
their suspicions. They have always had a monogamous
relationship and never felt the need to use a rubber
while fucking ass.
It came as a surprise to both of them when the
head of their department invited them to him office
during his office hours. He was very polite when he
invited them to have a seat. It came as a shock when
he confronted them about their relationship and what
they planned to do after graduation.
They were dumbstruck to discover that he knew
about what they had been doing for years on their
weekends. He did not divulge how he knew. It was
simply a statement of fact, without reproach. Then
he shocked them by suggesting that they think about
pursuing a teaching position with the school.
If you enjoyed the story and have a story you want
me to write about your introduction to the world of
male sexuality, please send your outline to
whitewold999@icqmail.com